Acetic Anhydride → HCID 20523559, compound

HRID 1413890Notes

Reaction equation

HRID 1413890 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[C:11]([C:13]1[CH:21]=[CH:20][CH:19]=[CH:18][C:14]=1[C:15]([OH:17])=[O:16])=O)=[CH:8][C:7]([O:22][CH3:23])=[CH:6][CH:5]=2.[CH3:24][N:25]([CH3:35])[C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([N:32]([CH3:34])[CH3:33])[CH:27]=1.C(OC(=O)C)(=O)C>>[CH3:33][N:32]([CH3:34])[C:28]1[CH:27]=[C:26]([N:25]([CH3:35])[CH3:24])[CH:31]=[CH:30][C:29]=1[C:11]1([C:10]2[C:9]3[C:4](=[CH:5][CH:6]=[C:7]([O:22][CH3:23])[CH:8]=3)[NH:3][C:2]=2[CH3:1])[C:13]2[C:14](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:15](=[O:16])[O:17]1

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 897151,3-Benzenediamine, N1,N1,N3,N3-tetramethyl-HCID 204713452-(5-Methoxy-2-methyl-1H-indole-3-carbonyl)benzoic acid

Product 1

HCID 20523559HCID 20523559, compoundYield 91.5%

Procedure

A mixture of 2.0 g (0.006 mole) of 2-[(2-methyl-5-methoxy-3-indolyl)carbonyl]benzoic acid, obtained as described in part A above, 1.1 g (0.0067 mole) of N,N,N',N'-tetramethyl-m-phenylenediamine and six ml of acetic anhydride were interacted at 50°-55° C. in a manner similar to that described in Example 2, part B to obtain 2.5 g of 3-[2,4-bis(dimethylamino)-phenyl]-3-(2-methyl-5-methoxy-3-indolyl)phthalide (Formula III: R0 =R1 =R2 =R3 =R6 =H; R=R5 =CH3 ; R4 =N(CH3)2 ; Y1 =OCH3), as a light pink-colored solid melting at 196°-198° C. with decomposition. The infrared spectrum, showing a significant maximum at 1740 cm-1 (C=O; s) and the nuclear magnetic resonance spectrum were in accord with the structure. A toluene solution of this product spotted on a phenolic resin coated paper developed an intense violet-colored image.

Workup

  1. customobtained
  2. customwere interacted at 50°-55° C. in a manner

Sources & evidence

ORD record
ord-6917e60ce92040be8069a2fdf7b5358b
Source dataset
uspto-grants-1981_02
Patent number
US04251446

Reaction notes

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